Pros & Cons of Sleeping With Derek Hale
by keep my issues drawn
Summary: "You need to make a list!" Scott tells him. "Pros and cons. Of sleeping with Derek." "Oh, how very 'Ross and Rachel'."
1. Part 1

Stiles is pretty sure he's going insane. And so he does what he always does when he feels like that — he calls Scott. One of the many benefits of your best friend being a werewolf is that they take as little time as possible to get to your house, which is always comforting. One of the downsides is that Stiles tends to get mixed up in things that are extremely hard to get out of — and things that he's not even sure he wants to get out of. Sometimes that means being known as an enemy by an Alpha pack, but sometimes it's things like the fact that he's sleeping with Derek Hale and he has feelings for him but doesn't know whether Derek feels the same. It bugs him that he doesn't know what it means. Part of him is yelling "who cares what it means, he's _Derek Hale_!" but Stiles also has a part that wants to figure out the meaning of it. That's what he tells himself, anyway, but really it's the fact that Stiles wants more than Derek ever will. And that really, really sucks. Which is where Scott comes in.

It's probably not the best idea to ask Scott over when Stiles needs a bit of help with figuring things out, he thinks, but regardless of that, Scott's his best friend and it always helps to have his opinion on things. It's also vastly entertaining slipping details of his sex life into the conversation to see just how grossed out Scott can get.

Five minutes and fifty eight seconds after Stiles hangs up on Scott, his bedroom door swings open and Scott flops himself down next to Stiles on the bed.

"Is this a Derek thing?" Scott asks, sighing slightly.

"Your skills of observation are rivalled by none." Stiles replies dryly. He pauses for a moment. "I don't know what I want to do with Derek."

"Other than fuck him?" Scott asks.

"More like have him fuck me, but yeah. I don't know if I can do it anymore."

"Please don't use the word 'do' right now." Scott says.

"I hate you." Stiles says, not really putting much energy behind it at all.

"Why don't you want to..." Scott pauses. "um, do it, anymore."

"Because I'm an idiot." Stiles begins. "And I don't know if I can do this if all he wants is sex and I want more."

A silence fills the room for a moment. Stiles looks at his knees. He's almost embarrassed, but this is Scott; he knows everything about Stiles. It can kind of suck for the both of them that they tell each other everything sometimes (namely when one of them divulges too much about their sex life) but neither of them would change it for the world.

"And you don't know what to do?" Scott asks.

Stiles nods in response, turning to look at Scott, as though expecting some wisdom to explode from his friend that will suddenly solve everything. However, such wisdom doesn't come out, but something else entirely does.

"You need to make a list!" Scott tells him. Noting Stiles' confused look, he continues. "Pros and cons. Of sleeping with Derek."

"Oh, how very 'Ross and Rachel'." Stiles remarks.

Scott stares at him for a moment but carries on. "Come on. It'll work."

"What if he finds it? I don't want to mess this up." Seeing Scott's confused look, he continues, "I mean, I don't know if I want to mess this up. I want to keep my options open though because if I mess it up and it turns out I don't want to mess it up then I'm gonna be really pissed at you for making me mess it up."

Scott stares at him incredulously. "You're insane. He won't find the list."

Stiles lets Scott drag him over to his computer and seat him on the computer chair. Following his lead, Stiles opens up a Word document and stares at it blankly for a moment. Stiles begins typing, but stops abruptly after writing 'Pros and Cons'

"What am I titling this as?" he asks Scott, turning to see him leaning over his shoulder.

"Your choice." Scott tells him, leaning over his friend's shoulder to see what he types.

Tentatively, Stiles types 'of', before pausing and sighing. "Am I going with 'fucking', 'sleeping with' or 'having sex with'?"

"Sleeping with is less explicit." Scott puts across.

Stiles turns around and stares at him. "Yeah, that'll come in handy when all the five year olds I know are reading it."

Nevertheless, he finishes typing and pushes his computer chair back — and he swears blind if it weren't for the fact that Scott had werewolf reflexes his friend would be on the floor — to look at the screen.

'Pros & Cons Of Sleeping With Derek Hale'

"Starting with Pros?" Scott asks. Seeing Stiles nods, he continues speaking. "Come on then: there's gotta be some reason you're fucking the guy."

"Again, he's fucking me." Stiles corrects him. "But right now I _am_ imagining Derek as a power bottom."

Scott elbows him sharply in the ribs, ignoring Stiles' wince. "We've been through this. Too much information?"

"Like you don't let Allison dominate you." Stiles scoffs. He doesn't need to turn around to see that Scott's looking extremely uncomfortable.

"I'm leaving." Scott says, getting up as if to go — even though both of them know it's just an act.

"Come on!" Stiles yells. "I need your wonderful wolfy advice and shit." he trails off.

"Fine." Scott tells him. "But we're not talking about our sex lives."

"That's kind of why you're here right now..." Stiles tells him. "To help me with my sex life?" Seeing Scott's look he jumps from the chair. "Not like that."

Scott joins him back by the computer as Stiles slides back onto the chair again. "Pros, then?" Scott says.

"There's the whole thing where Derek fucks me and it's the best sex I've had since... ever." Stiles says. "How do I write that down?"

"Derek fucks me and it's fucking awesome?" Scott suggests.

Stiles sends fake betrayed eyes at Scott. "He _does_?"

"Hilarious. Write it down."

Stiles makes a big show of sliding the computer chair closer to his computer and typing without looking at the keyboard. He turns back to Scott, looking like an eager puppy. Scott can't quite hold back a smile.

"You really, really like him, don't you?" Scott asks, although it's more of a statement than a question.

Stiles nods. "I didn't mean to."

"It's not an accusation."

"It should be." Stiles tells him. "All this was meant to be was sex. That's what we agreed on. And now I'm fucking it up because I have _feelings_ for him."

"It's not your fault the tin man has no heart." Scott says, trying to console him.

"Why couldn't I have been his wizard?" Stiles moans.

Scott raises an eyebrow. "Because Derek's a hopeless case."

"Fuck Derek Hale." Stiles groans. His eyes light up a bit. "But also _fuck_ Derek Hale, y'know?"

"Why are we friends, again?" Scott laughs.

"Because you're a loser and I'm nice enough to up your street cred." Stiles tells him. "Come on, we need more pros."

"Hopefully pros that don't involve the word 'fuck'." Scott says.

Because, seriously.

* * *

Derek really regrets the fact that he decided he'd be okay with living with Cora and Peter. He misses having his own space, even if it was a half burnt down house that looked like it came straight out of a horror movie. The thing is, nothing is private any more. If anything can be said about Derek Hale, it's the fact that his family seem to be incapable of staying out of his business.

In the morning he's greeted by Cora. "Doing anything with Stiles today?" she asks.

"You know, normal people say 'Good morning'." he grumbles as he fixes himself a cup of coffee.

"And by doing anything, I mean sexual acts." she replies dryly. To be honest, with her sarcasm, he's surprised she's not the perfect match for Stiles. Although, he wouldn't exactly say he's disappointed.

"Move." he says, trying to get to the fridge.

"You're avoiding the topic." Cora laughs, moving away so Derek can grab some milk. "Fine. It's none of my business. But, really, when are you gonna tell Stiles you have feelings for him?"

"I would say never, seeing as I don't." Derek growls.

"You're so in denial it physically hurts me, Derek." Cora tells him. "Go get fucked."

There's a part of Derek that's tempted to tell Cora that, actually, it's more correct to say he does the fucking, but all that would do is provide his little sister with more ammunition that Derek can fight off. She's right, of course. He does like Stiles. But all Stiles wants is a friends with benefits type relationship; and they don't really even have the whole 'friends' thing quite worked out yet. What they do have, though, is awesome sex and Derek is not going to mess that up because of feelings. He sends another death-glare at Cora before he leaves the room, armed with coffee. He hears Peter enter the kitchen and begin talking to Cora in hushed whispers. Derek's pretty sure Peter knows he can hear him anyway; he's a werewolf, for fucks sake.

"STILES IS _NOT_ A TWINK." he yells through the door, before downing the coffee and heading off to have a shower. And if he thinks about Stiles calling himself Derek's twink and he has to stop himself from moving his hands a little bit lower? Nobody needs to know.

* * *

Two hours have passed and Stiles' 'Pros' list consists of 'Derek fucks me and it's fucking awesome' and several variations of Derek's name in capital letters. Trying to look busy as Scott comes into the room with two cups of coffee, Stiles types frantically. Scott puts down the coffee and leans towards the screen.

"Because Derek Hale," he reads out loud, shooting a look at Stiles to see if he's for real, "I'm pretty sure all your reasons are the same point written in different ways."

"You have a point," Stiles says. "He's _Derek_."

"There must be other good points." Scott replies.

"Sometimes he stays for a bit and cuddles. And if I'm really lucky he makes me coffee." Stiles offers.

"You ever make him coffee?" Scott asks.

"Dude, I don't want to poison him!" Stiles huffs. "Also, the fact that he has claws is an added bonus."

Scott makes a disgusted face. "I don't even want to know."

"We're thinking up pros and cons here, I can't leave some out so you're not uncomfortable." Stiles pauses. "Oh, I can add that — mentioning what I do with Derek makes Scott really uncomfortable."

Scott glares at him as Stiles types the new things on the list. Finally, they're being productive. Although perhaps most people's idea of productivity is not writing a list that consists of Pros and Cons of sleeping with a werewolf. Then again, most people are stupid, boring, or don't believe in werewolves.

"Is 'Cons' gonna be a bit quicker to write?" Scott asks. "I love you, but thinking about you having sex with Derek for another two hours might just kill me."

"This is payback for hearing about you and Allison." Stiles fires back. "And, you know, it's not just 'about' it. I don't want to hear you having sex while I'm eating my cereal."

"That was one time!" Scott yells, half laughing. "Fine. I deserve this."

"Revenge." Stiles says.

"Please don't fake an evil laugh, I will k—" Scott is cut off by Stiles maniacally laughing. Scott throws himself onto the floor. Fuck Derek Hale. But, really, not in the way Stiles does.

When Stiles stops sounding like a pantomime's main villain, the boys turn back to the list. Stiles types 'Cons' and stares at the screen for a while before Scott pushes him on.

"You've already told me the cons. Just write them down."

Stiles types, more slowly this time, as if the act of putting them down on paper will make them more real. Scott reads to himself as Stiles types. Even though Stiles is typing more slowly this time, he doesn't stop in between points. When he's done, he stares at his computer screen,

"Do you think I should print it?" he asks Scott.

Scott's too busy reading through the points. "What?"

"Print it." he says, making weird hand motions in the direction of the printer."Should I?"

"May as well." Scott shrugs.

Stiles presses the print button and both of them lapse into a comfortable silence as the list prints. Neither of them notice the dark shape outside the window.

* * *

Part Two coming up soon with Derek POV and smut. Motivational reviews will make me update more quickly. ;)


	2. Part 2

Sometimes Derek worries about how used he is to climbing through Stiles' window. Although, it's probably less of a worry and more of an 'Oh my God, what am I doing with my life?' kind of thing. He's lost track of the amount of times he's climbed through Stiles' window. To be honest, the main reason he neglects the doorbell is that he enjoys Stiles' shocked expression when Derek takes him by surprise. The only problem is, Derek usually counts on the fact that Stiles will be alone.

Derek drops through the window. It kind of really sucks that Scott is the first one to notice him. He locks eyes with Scott, hoping he's not going to make some kind of inappropriate comment.

"Is this some kind of booty call?" Scott asks, causing Stiles to cough, choke, spin around on his computer chair and nearly fall off. _Attractive,_ Derek thinks wryly, watching Stiles seat himself back on the chair looking extremely red.

"That would imply that he actually called me in advance." Stiles chokes.

For some reason, both Scott and Stiles are looking towards the printer. It could be because of the really annoying noise it's currently making — seriously, Derek wouldn't be surprised if it started twitching and fell to the ground — but he's not so sure. Scott and Stiles may be idiots, but they wouldn't look guiltily at a printer that was making too much noise.

"You need a new printer." Derek remarks, laughing to himself at Stiles and Scott's worried looks.

Stiles scoffs, "Says the guy who lived in an abandoned house in the middle of the woods for two years."

Derek glares at Stiles and Stiles glares right back. Come to think of it, this happens a lot.

"I can, uh, leave?" Scott says hopefully. Both Stiles and Derek snap around to look at him. "Yeah, I'm gonna leave."

"Don't forget to take your homework." Stiles yells at him, indicating his head towards the printer like he thinks Derek can't see him. Derek will definitely try and find out what it actually is later. Maybe have sex with Stiles first, though.

Scott smiles brightly to indicate he's understood and grabs the paper before getting out of the room as quickly as possible, which is pretty quick. Derek is left alone with Stiles in the room — finally. There's an awkward pause which entails both of them staring at each other's lips; which, come to think of it, also happens a lot. That is, until one of them decides to take initiative and just fucking kiss the other. Derek supposes it's up to him to take initiative today.

He doesn't really think about the fact that he's crossing over the room before he's practically straddling Stiles in his chair. He presses his lips roughly to Stiles' lips and fists his hand into Stiles' hair, feeling for when Stiles opens his mouth slightly, before Stiles pulls back slightly.

"Is this how you say hello?" Stiles asks. "Because I'm thinking you should just say hello, like, forever."

"Shut up and kiss me." Derek growls; Stiles hastening to obey.

With Stiles, Derek's never really sure if they're kissing or wrestling. Stiles is still on the chair but it keeps tilting precariously and if Derek wasn't so focused on Stiles he'd probably be a bit worried that the whole thing would tip over. He can feel Stiles' hands on the base of his neck, Stiles' lips and tongue pressing against his own and he leans forwards even more—

And the chair falls. Derek sees Stiles' shoulder fall back onto the mouse and then the printer starts whirring. It feels like a cartoon, the two of them suspended in the air before they fall to the floor, Stiles somehow twisting enough that his head doesn't knock against the computer table and Derek not doing anything at all because seriously what the fuck.

They land on the floor, Derek on top of Stiles and Stiles looking stunned from the fall. Derek rolls over onto his side to join Stiles on the floor.

"Serious case of déjà vu right now." Stiles says. "Is that just me?"

Derek lazily cuffs him on the arm.

"Ouch."

The two of them lie there for a moment, the sound of the printer in the background. Derek remembers wanting to see what it was. He stands up, Stiles groaning at him to stop moving, and walks over to the printer.

"Why does Scott's homework have my name on it?" he asks.

Stiles looks shocked, worried and terrified all at the same time. Although, maybe it's just one emotion that Derek doesn't know of yet. "Don't read that."

Derek begins reading, his face completely emotionless. "Pros and Cons of Sleeping With Derek Hale." he reads aloud.

Stiles looks as though he's torn between bolting from the room and grabbing the list from Derek, but he does neither. "Don't be mad." he says. "Please don't be mad."

* * *

Stiles feels like hours past before Derek answers, but in reality it can only be seconds. He can't believe his life is turning into an episode of Friends (although Stiles has always pictured himself more as Rachel than as Ross). He mentally makes a note to never take Scott's relationship advice ever again.

"Why would I be mad?" Derek asks.

Stiles pauses for a moment, wearing his best 'are you for real?' expression. "Dude, have you ever watched Friends?"

"The negatives aren't about me, stupid. They're about you." Derek tells him. Stiles has always known Derek to be emotionally stunted but it surprises even him how long it takes Derek to speak again. "I..."

"Spit it out." Stiles urges him on, wishing that he was falling in love with someone who could say what they were feeling without wearing a look that made them look constipated.

"I like you, you idiot." Derek blurts out, a flash of something that looks like regret showing on his face for a second. "I didn't want it to come out like that."

The only thing Stiles can think is how bloody _typical_ this is. To be honest, he doesn't even know how either of them function when they're both so fucking clueless and not exactly gifted in the romance department. But, then again, Derek's said it and Stiles can only really reply in one way.

Before he knows it, his lips are on Derek's and they're fighting for dominance — a fight that Stiles is pretty sure he isn't going to win but takes part in anyway. It's not as though losing is a hardship or anything. Thankfully, the bed isn't too far away and so they manage to get there pretty quickly, shedding clothing as they go.

"I can't believe how stupid we are." Stiles breathes, snatching some air before leaning back into Derek.

"Speak for yourself." Derek growls playfully, his claws appearing and scratching Stiles slightly. "Sorry." he grunts.

"Did you even fucking read the list?" Stiles asks. "That's a definite pro."

At this point, the two of them are shirtless, Derek on top of Stiles and the only word to describe it is perfect. Hands trembling, Stiles reaches down to Derek's trousers and unbuttons them, knowing that although they've done this before, it's different this time. Derek shifts a little, helping Stiles take his own trousers down until all that stands between them is their boxes.

"I feel like I should make a list." Derek teases, his hand moving down to remove Stiles' boxers.

Stiles moans against him. "Only if you get completely naked _right now_." he orders, Derek hastily complying and pushing Stiles down onto the bed, straddling him, his cock already hard. "Pros first?" Stiles says meekly.

"Can I say 'I fuck Stiles and it's fucking awesome?'" Derek says mockingly.

Stiles flushes bright red. "Scott came up with the wording."

"Please don't mention Scott while I'm trying to have sex with you." Derek cringes.

"Noted. Maybe you should get on with the whole having sex with me thing?" Stiles pushes. Derek's lips are on his neck and, okay, that's good too. Stiles will definitely have a bruise in the morning, and his only reaction is God, yes. Everyone who has a thing for marking should definitely date a werewolf at least once in their life, Stiles decides.

"Are we dating now?" Stiles blurts out. "I mean, we don't have to go out. We can do domestic shit like order Chinese and stay in watching dramas on Netflix and we can cook together maybe and—"

"Yes, God." Derek tells him, pulling away for a second to grab some condoms and lube from Stiles' bedside drawer. "That'd be a pro to add to my list."

"Along with what, exactly?" Stiles asks coyly. He's getting a list out of Derek if it kills him.

"Your face." Derek teases. "That's pretty perfect. And the way you kiss me." Okay, so maybe Derek can do romance. Stiles watches as Derek lubes up his fingers, tensing slightly in anticipation, even though he knows he should relax.

Derek slides a finger in and Stiles lets out an involuntary moan. Still, it's better than their first time when Stiles squeaked slightly — even though Derek swore that it was okay, once he managed to stop choking on his laughter. Derek smiles at the noise and begins opening Stiles up, Stiles' legs moving out further for him.

"You let me make you coffee." Derek tells him as he pushes in another finger, scissoring them slightly inside of Stiles. "And you're smart. You notice things."

Stiles is almost silent beneath him, apart from the breathless gasps that Derek always manages to get out of him. He wants to try and formulate a response but he has no idea what he should say. "I am pretty smart." he murmurs. Hearing Derek's laugh, he tries to look offended. "Your fingers are inside me, I'm not very coherent right now!" he says indignantly.

"Want to change that?" Derek growls. Much to his displeasure, Stiles bursts out laughing. "What?" Derek demands.

"That line makes me feel like I'm in a bad porno." Stiles wheezes.

"Shut up, Stiles." Derek says, pulling his fingers out from Stiles and grinning slightly at the noise Stiles makes when he does.

"Do I talk too much during sex?" Stiles asks cheekily as he watches Derek tear open a condom.

"You talk too much, period." Derek grunts. Stiles is about to formulate a disgruntled reply when he feels Derek push into him. "That shut you up."

Stiles doesn't even bother talking, only twists his hands into Derek's hair and moves alongside him, noticing how their bodies move in sync with each other, Derek's lips wandering and Stiles battling between lying back and feeling Derek and summing up the strength to tilt his head up slightly to watch Derek at it. In the end, he settles for pulling Derek back up to his lips and kissing him. Stiles' inner monologue seems to turn into a poet and he thinks things like how it seems like when he's with Derek, nothing else exists, and how he wouldn't give up what he has with Derek for the world. He wonders if Derek thinks the same, or if Derek has some kind of angsty, 'woe is me' inner voice going on. He makes a mental note to ask.

"You're pretty quiet." Derek observes. Yeah, there's definitely a 'woe is me' inner monologue going on in there.

Stiles laughs a little and draws him back into a kiss, feeling Derek thrust inside of him, once, twice more, and feels Derek come and himself follow seconds after. Derek pulls out slowly and collapses on the bed next to him, chest heaving. Stiles' hand moves down to Derek's and his fingers brush against Derek's hand before he feels the older man hold his hand tightly.

"We should probably shower." Derek murmurs.

Stiles stares at him incredulously. "And get out of bed? We should just cuddle instead."

And although Stiles hears a sigh from beside him, as Derek curls himself around Stiles, he's pretty sure that there are no complaints from either of them.

* * *

Stiles wakes up to see Derek standing at the foot of his bed. Blearily, he rubs sleep from his eyes, shifting a bit in discomfort as he regrets not showering last night.

"I'm getting Twilight flashbacks." he tells Derek. "You're doing that creepy stare thing again."

Derek is holding a piece of paper, he now realises. Stiles leans up on his elbows to try and get a closer look. "Is that..?"

"I wrote the cons while you were asleep." Derek says, somehow managing to keep a straight face whilst doing so, even as Stiles falls back onto the bed.

"It's too early for this." Stiles groans. "And I have dried come, like, all over me."

Derek makes a disgusted face. "You should have showered." he tells him. "That's one of your cons. You refuse to move after sex."

"I do sometimes!" Stiles tells him. "If it's urgent."

"Or for a second round." Derek adds dryly. "Your Dad is the Sheriff and that scares me."

Stiles opens his mouth as though he's about to object, but after a few seconds closes it again. He tries to ignore his resemblance to a fish blowing bubbles, but that's never been an easy thing for him.

"You tell Scott everything." Derek tells him. "It's weird."

"I don't tell Scott everything." Stiles replies. "I tell him important things about my life. And all the details. Okay, so maybe I try to scare him by talking about my sex life but that's only revenge for overhearing him having sex with Allison one time and that was fucking—"

"And you talk too much." Derek says, a smug look on his face.

Deciding there's only one way to shut the older man up, Stiles leaps out up onto his feet and, standing on the edge of the bed, kisses Derek hard. He wraps his legs around Derek's waist and feels Derek kiss him back roughly.

"Maybe you can get up in the mornings." Derek murmurs. "I don't think I've ever seen you do that before."

"I probably missed some cons off the list." Stiles mutters. "Like the fact that you're somehow alive and awake in the mornings. How are you even human?"

"Technically, I'm not." Derek tells him.

Stiles elects to ignore Derek's response, even though he's correct. "And you're pedantic and grumpy and you're probably too old for me."

"Definitely too old for you."

"I don't care." Stiles says, letting Derek push him up against a wall and kiss him until his lips are sore and bruised. And, wow, there certainly are a lot of pros to dating a werewolf. Especially Derek Hale.

* * *

sorry i took so long to update, guys! please drop by a review or favourite if you enjoyed. :)


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